At Apple’s recent special music event, Steve Jobs announced the release of another iteration of Apple’s venerable media player, media store gateway, device manager juggernaut iTunes — iTunes 10, to be exact — with yet another feature shoehorned in: Ping, Apple’s music-oriented social network. I have little interest in Ping itself — okay, no interest at all — but this gives me the opportunity to discuss something that has been on my mind for a while: why I like — nay, love — iTunes.

For the record, when referring to “iTunes,” I am referring to the application itself, the media player, not necessarily the iTunes Store, although they are so tightly integrated as to be sometimes indistinguishable.

When I tell people that I love iTunes, I often get raised eyebrows or looks of incredulity. This might be because iTunes has become so common and well-known that actually liking it seems redundant. It would be a bit like admitting to your friends that, after much consideration, you do indeed find paved roads much more convenient for automobile travel. Even if it’s true, who cares? Surely the individual espousing such an opinion is either completely out-of-touch with the rest of the world or holds his own opinions in much higher regard than those of his peers.

Or maybe it is because it has become fashionable to complain about iTunes. When anything becomes ubuquitous, be it Twitter, Crocs, or iTunes, it is accepted by most with blasé and the grumbling desire to be rid of it. Since a large number of people use it in some capacity, iTunes is no longer a choice for most consumers. It’s just the thing you need to make your iPod work. What’s to like?

When described as just a media player, it’s easy to understand why iTunes is sometimes berated. After all, if you are just trying to play a few MP3s or watch a video clip, using iTunes is like shoving your head into a vice to pop a zit. However, when you need to manage a large and varied digital media library, and you need to synchronize this library with one or more portable digital media devices (iPods or iPhones, naturally), nothing on the market comes close to competing with iTunes.

A lot of criticism regarding iTunes is actually deserved. For example, a common complaint is that iTunes is slow, which is definitely true on Windows, at least it was the last time I tried it a few years ago, and is sometimes true on a Mac. Others claim that iTunes is bloated, which it most certainly is (and the addition of Ping has exacerbated this yet again). Still others gripe because Apple refused to design iTunes as a native Windows application. Again, this is true.

Despite its flaws, I believe iTunes to be one of the best applications ever developed for any platform. iTunes occupies a difficult niche at the crossroads of the digital and physical worlds, a precarious place where many other pieces of software often fail miserably. But, before I can explain why I think iTunes performs so well, I have to explain why so many other media players perform so poorly.

The Early Days

In the late nineties, storage capacity was growing, bandwidth was increasing, and the MP3 format had become commonplace. It was in this environment that Winamp stormed onto the scene and the digital media player became an indispensible piece of software for many, myself included. Prior to MP3s, my experiences with digital music were limited. I had kept a small library of downloaded MIDI files mostly for their novelty value — “Hey, wanna hear Axel F?” — and I had spent countless hours composing (tracking?) my own music using Scream Tracker (good memories, that), but that was pretty much it. Thus, before MP3s, I didn’t have much use for a media player. There just wasn’t anything to play, much less manage.

But Winamp changed everything and, have no doubt, it really did “whip the llama’s ass.” In its early years, there was nothing like it. Even the venerable Windows Media Player, which had existed in one form or another for years as a simple video player, did not compare to Winamp’s unique ability to organize and play music. Winamp’s surging popularity drew the attention of AOL who quickly snatched up Nullsoft, the company beind the media player. Like most Windows users, I relied on Winamp for many years, right up until I began using Linux in 2006.

By then, Winamp’s glory days had waned. It had long since become a bloated piece of nagware. Winamp’s UI had also suffered. Gone was the crude yet simple UI of yore. Instead, we now had the ability to “skin” the application. Unfortunately, all of the available skins made me want to wretch. Even the default skin was ugly, cluttered, and confusing. I have always hated when UI designers use theming as an excuse not to provide a good default. I don’t care if I can make my media player look like the cockpit of a B-2 stealth bomber, just give me a simple, clean UI.

I switched to Linux in 2006 and, considering the sad state of Winamp, I was eagerly looking forward to finding a replacement for it. For a while, Amarok addressed most of my needs. It was a fine media player in the Winamp tradition. But, by late 2007, Amarok had been suffering from the same bloat and lack of polish that affected KDE as a whole, so I tried numerous GNOME-based alternatives, Rhythmbox and Exaile being the most memorable.

Unfortunately, I never found a media player I really liked. It wasn’t because they couldn’t play music. That was the easy part. It was their poor UIs, their lack of attention to detail, and their inability to effectively organize and manage large digital libraries that I found most annoying.

Finding iTunes

Interestingly, although iTunes had been available for Windows users since 2003, I had never once tried it. I didn’t have much reason to. I didn’t own an iPod and I refused to buy DRM-laden music, which was all iTunes carried, on principle. At first impression, iTunes seemed like junkware to me. Whenever I downloaded the QuickTime player to my Windows machines Apple always tried to piggyback iTunes onto my download. In my experience, whenever a company is that eager to give away its software, you know it’s junk. It wasn’t until I switched to the Mac in 2008 did I really give iTunes a fair shake.

The more I played with iTunes, the more I realized how amazing it really was. Here are just a few of iTunes’s major achievements over its competitors:

The UI was clean, simple, and elegant. The next best UI I have
encountered was Exaile on Linux, albeit with a severe reduction in
functionality.

Although I resisted it at first, I was finally freed from having to
manually manage my music. Instead of creating directories for artists
and albums and then pointing my media player at these directories, I
just let iTunes handle the organization from the start.

Once I imported a song into iTunes, I could delete the original file.
This was unsettling at first but, once I got used to it, I enjoyed the
sense of freedom that it gave me: “Don’t worry, iTunes will take it from
here.”

Changes made to a song’s metadata automatically updated the respective
file structure if necessary. For example, if I moved a song from one
album to another, iTunes moved the file automatically. I had nothing
more to do.
Furthermore, this underlying file structure meant that, if I wanted to,
I could easily locate the actual physical file.

Smart Playlists were a welcome addition. You would think that something
so obvious would have been common in all media players.

Cover Flow provided a unique, elegant, three-dimensional way for me
to view my albums. Since going digital, I hadn’t realized how much I
missed the feeling of “flipping through” my albums.

iTunes offered a ton of metadata options, allowing it to gracefully
handle albums by single artists, compilations, multi-disc albums,
podcasts, audiobooks, and more.

I could sort music on any number of fields, including “Album by Artist,”
which I am quite fond of and have rarely seen duplicated in other media
players.

iTunes was the first media player I ever used that correctly handled
album artwork. Every other media player claimed to but, in my
experience, not one succeeded.

Clever and useful library searching. I remember struggling with this
with Winamp. It was sometimes difficult to know which songs you had
because there was no reliable way to search your library’s metadata.

Once the DRM was gone, I could buy songs directly from the integrated
iTunes Store.

When ripping CDs, iTunes provided me simple options. Even as a geek, I
had a difficult time determining the minute differences in lossy
encoders, bitrates, and licenses presented to me by other applications.
Presenting these options as a simple “Low, Medium, High” list was a vast
improvement. I can easily understand that high quality requires more
storage space, but I can’t easily understand why I would choose LAME
over MP4/aacPlus at 128kbps VBR versus CBR, etc.

iTunes seamlessly provides two-way synchronization for music and
playlists to an iPod with just a few clicks. If I rate a song on my
iPod, the rating is carried over to iTunes on my computer the next time
I sync. This is important because, with Smart Playlists, your
preferences might change over time, and it’s annoying to have to make a
mental note to “Rate this song down a star when I get home.”

Library sharing. While this feature could definitely use some work,
it is very easy to set up library sharing over bonjour on a local
network.

Uh oh. Was your sync was interrupted? On many media players, this can
be anything from a minor annoyance to a disaster. On my Sansa SanDisk,
I once interrupted a sync and some metadata must have become corrupt, so
I ended up scouring the web for how to reconfigure my MP3 player. It
sucked. With iTunes and an iPod, this type of corruption is almost
unheard of.

Frankly, after using it for a few weeks, I couldn’t believe I had ever used anything else. Of course, as with all software, there were drawbacks. Here are a few of them:

iTunes never has handled streaming radio very well. Unless your choice
of radio station is already in Apple’s default list, it can be a real
pain to add a new station.

iTunes is slow to start on all platforms. See “iTunes on Windows” below
for a more detailed explanation of the problem.

Limited encoder selection. As I mentioned above, this can also be
interpreted as a feature since limiting choices makes the process
simpler for most users. Power users should definitely go elsewhere for
advanced ripping and encoding options.

In true Apple style, iTunes will only play a handful of the most widely
used file formats. Apple doesn’t typically waste time, energy, or money
trying to please everyone. If you aren’t using the most popular formats,
namely MP3, AAC, or Apple Lossless for music, you’re out of luck.
Fortunately, it is possible to hack in support for other formats such as
FLAC and Ogg.

By offering a ton of metadata options, one has the tendency to want to
fill it all out. If this hasn’t been done already, it can mean many
painful hours of data entry.

Small changes in metadata can have weird effects. For example, if one
song has the album date off by a single digit, that song will
mysteriously disappear and be transported away into in a doppelganger
album.

iTunes on Windows

To be fair, iTunes on the Mac is different from what most people experience on Windows. On the Mac, iTunes is largely snappy, responsive, and is perfectly integrated into the hardware and the operating system. On Windows, iTunes is a gross imitation of a Mac OS X application. Apple didn’t even bother to redesign iTunes’s UI to match the platform, a condescending slap in the face to Windows users if there ever was one (but, since Windows has no unified UI and has historically had relaxed UI guidelines, I don’t think most people notice unless you point it out to them).

The worst problem with iTunes on Windows, however, is speed. With everything hanging from its neck from the notoriously bogged down iTunes Store to library sharing via Bonjour, which can be slow on large networks, it is no wonder that iTunes takes a while to start. Like all Apple software, it is designed for a Mac where, once started, it remains running in the background. This is different from what Windows users expect. Windows users have been trained to kill every unused application and service to keep their system from slowing to a crawl. When a Windows users sees mdnsresponser.exe and the Bonjour Windows service active, they freak out and kill it without really understanding what it is. They then gripe that iTunes has screwed with their computer and complain when library sharing or other services no longer work.

While this might sound like an overgeneralization, I have heard this exact argument more than once when speaking to people about iTunes. This is part of why Windows itself annoys me: it forces end users to grapple with concepts that should be abstracted from their experience. No one should be required to know how a Windows service functions just to use Windows. Yet, in many cases, users are sometimes required to manually tweak their systems in a way that assumes this knowledge.

Because iTunes is designed differently than most media players, Windows users tend to use it differently from most Mac users. Generally, one shouldn’t use iTunes like Winamp or VLC. In other words, clicking on a filename just to play a song or video clip in iTunes is really kind of silly. Sure, iTunes can do this, but it is designed to manage large media libraries, to sync with mobile devices, and to act as a gateway to the iTunes Store.

When someone says to me that iTunes is slow to launch, I find myself thinking: “When was the last time I actually launched iTunes? Must have been the last time I rebooted. That was, ummm, a month ago?” For Windows users, this kind of application longevity is almost unheard of. Launching and closing iTunes are regular, painful experiences not to be discounted.

iTunes Bloat

With iTunes, Apple has earned a lot of money and a lot of mindshare. In the minds of most, iTunes the application and the iTunes Store are one and the same. From Apple’s perspective, this is probably for the best. Regardless of which head of the bicephalic monster we are talking about, virtually everyone has heard of iTunes. But this presents a problem for both Apple and for consumers.

Apple doesn’t want to complicate things. And neither do consumers. So, when Apple wants to promote a new feature, it is going to end up in iTunes. After all, we already have it installed, we already know what it is, and we’re already using it. Why introduce a new piece of software to do something that iTunes is already designed to handle? Take iBooks for example. If you were Apple — or, hell, if you were you — would you prefer to install another application to manage your digital books, or would you just rather add a tab to iTunes?

This means that, with each iteration of iTunes, it gets more bloated. Here are just a few examples of how iTunes has outgrown the boundaries its original domain of music (and related features like playlists and streaming Internet radio) and iPod syncing:

the iTunes Store

Podcast support

iTunes LPs, iTunes Extras

iTunesU

Photo and video support

Library sharing via Bonjour

iPhone activation

Apps management

Ringtones

iBooks (non-audiobook book and PDF support)

Ping

For any software geek, bloat is a bad thing but, sometimes, the alternative is worse. The real key to understanding iTunes bloat is in the knowledge that iTunes is not just a media-player, it is a bridge between the physical world — the one we and our iPods occupy — and the world of digital media, from which our music and movies and apps spring forth. By acting as a bridge for consumers, iTunes simplifies an insanely complex task: quickly and easily connecting our eyes and ears with intangible media stuff.

A Bridge Between Physical and Digital

Before buying an iPod, I tried a handful of different media players. I hated all of them. The hardware was usually fine but the software was a nightmare. In fact, in one case, I had so much trouble with the software that the device was practically useless. And it is this junction, at the point where the hardware meets software for the end user, where iTunes truly shines.

In the early days — the FairPlay days — iTunes was not so much a luxury as it was a necessity. Apple needed to not only provide a way for users to sync their iPods with their computers, they also needed a way to reassure the frightened record companies that users were not going to pirate their music. iTunes seamlessly achieved both.

Not only could iTunes manage a vast library of digital media with syncing so precise that even one’s place in an audiobook was recorded on sync, it also provided a means to manage the RIAA’s useless but complex DRM portfolio. No other vendor was able to assure the RIAA that its DRM requirements would be met while satisfying consumers’ demand for digital media. It was a juggling act truly worthy of praise, even if you opposed DRM (as I did, and do).

This is iTunes’s real achievement: it opened the door to digital audio in a way that no one had done before. Consumers were confident that, by plugging in their iPod, their music would magically appear on the device. There was no crapware to install (other than iTunes itself, of course), or procedures to follow. It just worked.

The time is fast approaching when the intersection between the physical and the digital will have grown so thin as to be barely noticable, where wires will no longer be needed, and digital synchronization will happen with no user intervention whatsoever. Soon, your music, movies, photos, books, and other digital media will be either be streamed to the device directly from the cloud or will be managed in such a way that no intermediary will be necessary. I am willing to bet that, when Apple takes that step, iTunes will be behind the scenes making it happen.

Why it Matters

The world is becoming increasingly mobile, and software like iTunes is facilitating that change. I believe the lack of an iTunes competitor is one of the Android platform’s biggest disadvantages. Google is trying to leap over the need for iTunes by going directly to the cloud for everything, similar to what Microsoft did with its ill-fated Kin. But the infrastructure isn’t ready for this yet. With 3G technology, we simply don’t have enough bandwidth or throughput to push all of those songs, photos, and videos over the air. Even with WiFi, it isn’t simple to do right.

Just imagine Apple TV and Google TV duking it out. With Apple TV at least, the user can stream his iTunes library from a Mac, PC, or iOS device. From Google TV, this is all supposedly coming from the cloud, but we have yet to see how well this will work in practice. So iTunes is not only Apple’s not-so-secret Ace up the sleeve, it is becoming more relevant as our use of mobile devices shifts from casual entertainment to a necessity of modern life.